First Date
by SamA3642
Summary: Jay and Will's younger sister has her first date. How will they react? One shot


"The two of you will behave and be nice to him". Sky said sternly to her two brothers.

Jay and Will looked at their younger sister with an amused look on their faces.

"Sky we are always nice". Jay said.

"Yeah when you want to be, guys this is my first real date with someone who I really like so please for me be nice".

"Alright, Sky we'll be nice". Will said.

"Thanks, Will".

Just then there was a knock on the door she quickly fixed her light purple dress and went to go answer it when she opened it she had seen her date for the evening. His name was Jake, he was tall, built very well, had short sandy blonde hair, sparkling blue eyes, he was wearing a simple white button-down shirt, black slacks, he wore high top sneakers.

"Hi, Sky". Jake said with a shy smile.

"Hey, Jake come in I want you to meet my brothers". Sky replies.

The two young adults have entered the living room where the two brothers were quietly talking among themselves with Sky got their attention.

"Guys this is my date, Jake. Jake these are my two brothers Jay and Will". Sky says introducing the men.

"Hi". Jake said.

"How are you doing Jake?" Jay asked shaking his hand.

"I'm good".

"Let's have a chat Jake". Will said.

"Alright".

Sky shot her brothers a look 'Be nice' Will nodded as everyone took a seat, Jay took a chair from the kitchen just as Will did. Sky and Jake took a seat on the couch sitting across from the brothers.

"So Jake what is it that you do?" Jay asked.

"I'm a med student I hope maybe one day I'll be a doctor". Jake answered.

"Really? I'm a doctor over at Chicago Med, maybe I'll see you around sometime".

"Maybe".

Jake was starting to rub his hands in a nervous manner Sky then took one of his hands into hers.

"You nervous Jake?"

"No sir".

"So what are your intentions with our sister?" Jay asked.

"I really like Sky, I want to get to know her better. Then maybe if things go in the right direction I see myself having a future with her". Jake answered.

Sky looked over at Will giving him a pleading look, 'Make him stop'. Will then looked over to his brother telling him to end the conversation.

"One more thing before you guys go, Jake, I can already see our sister cares about you very much but I'm gonna make one thing clear. You hurt her, we hurt you. I'm a detective over at the 21st district I know things, don't think I won't ever find things out. And I will always be watching you. Everywhere the two of you go I'll be right behind you watching". Jay said to his sister's date in a serious manner.

"You have my word sir, I won't do anything to hurt your sister at all. I have two younger sisters myself and I would say the same thing to the guys they'll date when they get older". Jake said.

"Alright go on you two". Will said.

The two got up and Jake went out first while Sky stands behind with her brothers for a moment.

"Thanks, guys and Jay next time remember that it's not an interrogation". Sky said.

"I have to look out for you Sky". Jay said.

"Go on before you're late". Will said.

She then kissed her brother's cheeks then left out, shortly after that Will had gotten himself a beer from the fridge and put on a basketball game just as Jay put his jacket on and put his phone inside his pocket.

"Where are you going?" Will asked his brother.

"Out to get some more beer we're running low".

"Jay don't go and follow Sky on her date, she's an adult she can handle herself".

"Why would you think I'd be following her?"

"Because we're not running low on beer, you don't have a case tonight, so you're gonna follow Sky on her date to make sure she's safe".

"Is that a crime?"

"No but when or if Sky sees you she'll be pissed at you".

"Then let her be pissed at me".

Jay then left the apartment just as Will picked up his phone texting someone.

Meanwhile

Sky and Jake were at an Italian restaurant for the evening, when they arrived inside and got a table Jake had pulled the chair out for her.

"Thank you, Jake". Sky said, her cheeks were starting to blush as they turned a light shade of pink.

"Your welcome my parents are a bit traditional and you can say I picked up on it". He chuckled.

"You have. So what made you wanna become a doctor?"

"Ever since I was little I've always wanted to help people and when I become a doctor I can fulfill my dreams".

"I wanted to become a detective like my brother but he doesn't want me too, I don't blame him the things he sees on a daily basis".

The waiter soon came bringing their drinks then took their orders.

"I'll have the chicken alfredo". Sky said.

"I'll take the fettuccine alfredo". Jake said.

The waiter wrote it down and walked away leaving the two to talk, Jay was outside of the restaurant watching he saw that his sister and Jake got a table by the window. He got broken out of his thought by the sound of his phone, he saw it was Erin calling him.

-Hey, what's up? Jay answered.

-Where are you? Erin asked.

-I'm at home watching the game with Will, why.

-No, you're not, you're out spying on Sky while she's on her date.

Jay became confused on how his partner knew this. -How do you know that?

-I'm parked right behind you. Turn around.

He then turned to see his partner as she got out from her car and went to his, Erin got on the passenger side as she handed Jay a cup of coffee.

"Thanks. So did Sky send you?" Jay asked as he sipped some of the warm coffee.

"Will text me right after you left, he said that you were spying on Sky while she was on her date". Erin replied.

"It's not spying I just wanna make sure she stays safe that's all".

"I wish I could say I understand but you have to face it, Jay, Sky's an adult now she can handle herself. She's a big girl now and I'm pretty sure she knows that if she's ever in trouble she can always go to you or Will about anything".

Jay let out a shaky sigh. "Being a cop is dangerous we both know this and it won't be hard for someone to find things out about any of us. If anything ever happens to Sky I would never forgive myself".

"You guys aren't gonna lose her right now and you can't blame yourself if anything happens".

He knew that Erin was right and he was speechless at the moment. "You're right I think what just gets me is that all the cases we do". He managed to get out.

"It's alright to be scared, Jay. Look go home wait for her I'm sure she'll be ok".

"Alright, I'll go home".

"Good".

Jay watched his sister once before just as Erin got out and went to her car. He then pulled off heading home.

Once Sky and Jake were finished eating they went on a walk and got ice cream.

"Thank you, Jake I had a nice time tonight". Sky said.

"I'm glad you had fun maybe we can do it again sometime". Jake says nervously.

"I'd like that".

Jake then walked her home for the night, the two were standing outside of the apartment building. Sky then kissed Jake's cheek then he kissed her cheek.

"Next Saturday sound good?" Jake asked.

"Sounds perfect".

"I'll see you then".

Sky then walked into the building just as Jake began his walk home when the youngest Halsted made it to the apartment she quietly opened the door not knowing if her brothers were asleep or not. When she heard the tv she saw Jay watching an old game.

"Hey, what are you still doing up?" Sky asked.

"I waited for you". Jay answered.

"Everything alright?"

"Yeah".

"You're lying".

"After you left for your date I followed you just to make sure you were safe".

"I had a feeling I was being watched I just didn't know it was by you".

"Sky I just wanna make sure you don't end up getting hurt in any kind of way".

"Jay I'm not gonna get hurt I have you, Will, Erin, and everyone at the 21 watching my back".

"It's my job to watch out for you".

"You mean our job". Will said entering the room.

"I'm sorry our job to watch out for you".

"I know and I understand".

She then hugged and kissed Jay's cheek. "What was that for?"

"For always making sure I was safe".

She then did the same to Will before going to bed for the night, Will then quickly glanced at his brother before speaking. "By the way how'd you know where Sky would be tonight?"

"I have my ways".


End file.
